Benzyl chloroformate → HCID 22456632, compound

HRID 537733Notes

Reaction equation

HRID 537733 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH:20]1([Mg]Cl)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1>[CH:20]1([CH:7]2[CH2:8][C:3](=[O:2])[CH:4]=[CH:5][N:6]2[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 692784-MethoxypyridineHCID 178478990HCID 178478990, compound

Product 1

HCID 22456632HCID 22456632, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

4-methoxypyridine (17.56 ml, 173 mmol) in THF (577 ml) at −30° C. was added benzyl chloroformate (24.70 ml, 173 mmol) dropwise. Stirred at −30° C. for 30 minutes and then added cyclohexylmagnesium chloride (200 ml, 260 mmol). Stirred for 30 minutes at −30° C. and quenched with 1N HCl. Extracted 3 times with diethyl ether. The combined organic fractions were combined, dried (Naz SO4), filtered and the solvent was evaporated under reduced pressure. Purified on silica gel 30% EtOAc/Hexanes affording 35.25 g.

Workup

  1. stirringStirred for 30 minutes at −30° C.
  2. customquenched with 1N HCl
  3. extractionExtracted 3 times with diethyl ether
  4. customdried (Naz SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customPurified on silica gel 30% EtOAc/Hexanes affording 35.25 g

Sources & evidence

ORD record
ord-e9e486ace0f6481195ecec50a5002404
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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